4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-amine → [7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-amine

HRID 1262100Notes

Reaction equation

HRID 1262100 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.[CH3:21][N:22]1[C:27]2[CH:28]=[C:29]([NH2:32])[CH:30]=[CH:31][C:26]=2[O:25][CH2:24][CH2:23]1>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:32][C:29]3[CH:30]=[CH:31][C:26]4[O:25][CH2:24][CH2:23][N:22]([CH3:21])[C:27]=4[CH:28]=3)=[N:5]2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 225984224-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-amineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66710840[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-amine

Procedure

The titled compound was prepared in analogous fashion as Example 113 using 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine and 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylamine to give 645 [7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-amine as a brown lyophilate. LCMS (E/I+) 388 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.88 (d, 1H, J=7.5 Hz), 7.27 (t, 1H, J=8 Hz), 7.04 (m, 3H), 6.95 (d, 1H, J=3.6 Hz), 6.81 (d, 1H, J=3.8 Hz), 6.72 (d, 1H, J=8.5 Hz), 6.65 (m, 2H), 4.24 (s, 2H), 3.81 (s, 3H), 3.20 (s, 2H), 2.56 (s, 3H).

Sources & evidence

ORD record
ord-c6ea9904c5354b7cb6e31d2a218581ae
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…